The Best of Simon Doonan’s Halloween Costumes Since 1978

It takes just one look at Heidi Klum come late October to remember that the stylish and famous take Halloween very seriously. But it’s Simon Doonan, the creative ambassador at Barneys New York, who has been playing that game since long before people knew of him. He doesn’t throw his own party — and, in fact, he’s not even dressing up this year — it’s a somewhat quieter sort of costume confidence. So he decided to prove his mettle by sending photos to the Cut of his best costumes starting from back in the late seventies. From Wayne Newton on the weekend to a look that resembled Amy Winehouse before she was even born, click ahead for his highlights, plenty of drag, and some ideas you can steal for your own costume.

Photo: Courtesy of Simon Doonan

1978

“Dominatrix Doonan”

Photo: Courtesy of Simon Doonan

1982

“Predicting Amy Winehouse”

Photo: Courtesy of Simon Doonan

1983

“New Romantic”

Photo: Courtesy of Simon Doonan

1984

“Light-up outfit by my old pal Susan Nininger (she did Whitney Houston’s silver stage costume in The Bodyguard). This outfit had a huge battery pack, which is probably why I am sitting down.”